US2478377A - Preparation of esters of acids of phosphorus - Google Patents
Preparation of esters of acids of phosphorus Download PDFInfo
- Publication number
- US2478377A US2478377A US602413A US60241345A US2478377A US 2478377 A US2478377 A US 2478377A US 602413 A US602413 A US 602413A US 60241345 A US60241345 A US 60241345A US 2478377 A US2478377 A US 2478377A
- Authority
- US
- United States
- Prior art keywords
- acid
- ether
- phosphorus
- acids
- blown
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000002253 acid Substances 0.000 title description 20
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title description 14
- 229910052698 phosphorus Inorganic materials 0.000 title description 14
- 239000011574 phosphorus Substances 0.000 title description 14
- 150000007513 acids Chemical class 0.000 title description 11
- 150000002148 esters Chemical class 0.000 title description 9
- 238000002360 preparation method Methods 0.000 title description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 13
- 238000007664 blowing Methods 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 230000005484 gravity Effects 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 235000011007 phosphoric acid Nutrition 0.000 description 6
- -1 phosphorous Chemical compound 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YDHWWBZFRZWVHO-UHFFFAOYSA-N [hydroxy(phosphonooxy)phosphoryl] phosphono hydrogen phosphate Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(O)=O YDHWWBZFRZWVHO-UHFFFAOYSA-N 0.000 description 3
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 150000003016 phosphoric acids Chemical class 0.000 description 2
- 229940005657 pyrophosphoric acid Drugs 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- HLSUQUJDDMLNMX-CLFAGFIQSA-N (z)-1-[2-[(z)-octadec-9-enoxy]ethoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCOCCCCCCCC\C=C/CCCCCCCC HLSUQUJDDMLNMX-CLFAGFIQSA-N 0.000 description 1
- KLLYJHRGEWEZOP-QXMHVHEDSA-N (z)-1-prop-2-enoxyoctadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCC=C KLLYJHRGEWEZOP-QXMHVHEDSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- NKSOSPOXQKNIKJ-CLFAGFIQSA-N Polyoxyethylene dioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCOC(=O)CCCCCCC\C=C/CCCCCCCC NKSOSPOXQKNIKJ-CLFAGFIQSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- HGWAKQDTQVDVRP-OKULMJQMSA-N butyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCCCC HGWAKQDTQVDVRP-OKULMJQMSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940120693 copper naphthenate Drugs 0.000 description 1
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 1
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
Definitions
- This invention relates to the preparation of hitherto unknown esters of the acids of phosphorus and more particularly to the preparation of phosphated and phosphited compounds derived from unsaturated ethers.
- This invention has as its object to provide a process for producing certain new chemical compounds which are esters of acids of phosphorus.
- a further object is to provide new phosphated and phosphited compounds which are esters prepared from blown unsaturated ethers.
- a still further object is to provide improved phosphated and phosphited compounds having exceptional usefulness as surface-active agents, wetting, washing, and dispersing agents, and as lubricating, anti-static and conditioning agents for textile yarns, particularly those composed of or containing cellulose acetate and related cellulose derivatives. Other objects will appear hereinafter.
- reaction may be as follows:
- tion may be represented conventionally as follows:
- the unsaturated compounds selected for blowing such as dioleyl ether, ethylene glycol, dioleyl ether, diricinoleyl ether, propane-1,2,3- tricrotyl ether, sorbitol dioleyl, diallyl ether, dioxane dioleyl ether, etc.
- the unsaturated compounds selected for blowing are heated from to 200 C. (125-180 C. preferred) and air or oxygen is passed in until a product having the desired properties is obtained.
- the unsaturated compound is blown the iodine value and saponification equivalent rise.
- One skilled in the art can, by following the progress of the above constants, determine when to stop blowing the unsaturated compound so as to obtain a product that will readily react with an acid of phosphorus.
- any of the -ous and -lc acids of phosphorus may be employed for phosphating or phosphiting the blown compoundsin accordance with our invention.
- Typical examples of such acids are phosphoric acid, metaphosphoric acid, monosodium phosphate, pyrophosphoric acid, tetraphosphoric acid, phosphorous acid, hypophosphorous acid and pyrophosphorous acid.
- esters of acids of phosphorus prepared by reacting an -ous or -ic acid of phosphorus with a blown unsaturated ether.
- unsaturated ethers which can be used in practicing our invention are those having the followin formulas:
- R is an olefinically unsaturated hydrocarbon chain having 3 to 25 carbon atoms
- R is a low carbon atom saturated hydrocarbon radical
- n is a number from 2 to 3.
- Example 1 grams of dioleyl ether is blown with air at C. using copper naphthenate as a catalyst. When the specific gravity of the material has increased 0.07-unit 50 grams of phosphoric acid are added, the reaction mixture is heated on a the structure resulting from the blowing operato steam bath for 12 hours. The excess acid is removed by washing with water. The heavy viscous phosphated product that results is water soluble.
- Example 2 100 grams of ethylene glycol diricinoleyl ether is blown as in Example 1 and reacted with 60 grams of phosphorous acid at 100 as above. The heavy viscous product is washed with water. The resulting phosphorous acid ester is water soluble.
- Example 3 100 grams of propane-1,2,3,-tricrotyl ether is blown as in Example 1 until the specific gravity has increased 0.05-unit and then reacted with 50 grams tetraphosphoric acid as in the examples above. The excess acid is removed by Washing with cold aqueous salt solution. The product is soluble in water.
- Example 4 100 grams of tetrahydrofurfurylerucyl ether are blown as previously described until the specific gravity of the oil has increased 0.04-unit and reacted with a 1:1 mixture of phosphoric acid and pyrophosphoric acid. The product is worked up as above.
- the compounds of our invention have many valuable applications in industry. For example, they may be employed as surface-active agents, wetting, washing and dispersing agents. We have found them to have outstanding properties when employed as lubricating anti-static and conditioning agents for textile yarns, particularly those composed of or containing cellulose acetate and related cellulose derivatives.
- R is an unsaturated hydrocarbon chain of 3 to 25 carbon atoms in which the unsaturation is limited to olefinic unsaturation and R is a low carbon atom saturated hydrocarbon radical, and n is a number from 2 to 3, at from 50 to 200 C., until an appreciable increase in specific gravity occurs, and thereafter treating She blown other with an acid of phosphorus selected from the group consisting of phosphorous, phosphoric, pyrophosphoric and tetraphosphoric acids.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Description
Patented Aug. 9, 1949 PREPARATION OF cs'rans F ACIDS 0F rnosPnonUs Joseph B. Dickey, Rochester, N. Y., and James G.
McNally, Oak Ridge, Tenn., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Application June 29, 1945, Serial No. 602,413
4 Claims. (Cl. 260-461) This invention relates to the preparation of hitherto unknown esters of the acids of phosphorus and more particularly to the preparation of phosphated and phosphited compounds derived from unsaturated ethers.
This invention has as its object to provide a process for producing certain new chemical compounds which are esters of acids of phosphorus. A further object is to provide new phosphated and phosphited compounds which are esters prepared from blown unsaturated ethers. A still further object is to provide improved phosphated and phosphited compounds having exceptional usefulness as surface-active agents, wetting, washing, and dispersing agents, and as lubricating, anti-static and conditioning agents for textile yarns, particularly those composed of or containing cellulose acetate and related cellulose derivatives. Other objects will appear hereinafter.
These objects are accomplished by the following invention, which is based upon the unexpected discovery that if certain linear ethers derived from unsaturated alcohols containing the group are heated and then blown with air or oxygen until an appreciable increase in specific gravity of the compounds occurs, such compounds will react with acids of phosphorus such as phosphorous, hypophosphorous, phosphoric, thiophosphoric, and the various pyroand polyphosphorous and phosphoric acids. This is a most unusual phenomenon when it is taken into consideration that compounds containing the group I -o=osuch as oleic acid, butyl oleate, oleyl alcohol, carbitol oleate, ethylene glycol dioleate, and butyl ricinoleate, oleyl ether, allyl oleyl ether, and ethylene glycol dioleyl ether, do not add acids of phosphorus, such as phosphorous and phosphoric acids when mixed and heated therewith.
While we do not confine ourselves to any specific theory or explanation of the mechanism of the reaction involved when the unsaturated com-- pounds are blown as above described, the reaction may be as follows:
tion may be represented conventionally as follows:
n H n n c---c- HO-P -o-c o I on It will thus be seen that the phosphato or phosphito group adds to the carbon chain at the position originally occupied, before blowing, by an unsaturated linkage.
In general, the unsaturated compounds selected for blowing such as dioleyl ether, ethylene glycol, dioleyl ether, diricinoleyl ether, propane-1,2,3- tricrotyl ether, sorbitol dioleyl, diallyl ether, dioxane dioleyl ether, etc., are heated from to 200 C. (125-180 C. preferred) and air or oxygen is passed in until a product having the desired properties is obtained. -When the unsaturated compound is blown the iodine value and saponification equivalent rise. One skilled in the art can, by following the progress of the above constants, determine when to stop blowing the unsaturated compound so as to obtain a product that will readily react with an acid of phosphorus.
Any of the -ous and -lc acids of phosphorus may be employed for phosphating or phosphiting the blown compoundsin accordance with our invention. Typical examples of such acids are phosphoric acid, metaphosphoric acid, monosodium phosphate, pyrophosphoric acid, tetraphosphoric acid, phosphorous acid, hypophosphorous acid and pyrophosphorous acid.
In view of the foregoing explanation the compounds of our invention may then be regarded as esters of acids of phosphorus prepared by reacting an -ous or -ic acid of phosphorus with a blown unsaturated ether. Among the unsaturated ethers which can be used in practicing our invention are those having the followin formulas:
wherein R is an olefinically unsaturated hydrocarbon chain having 3 to 25 carbon atoms, R is a low carbon atom saturated hydrocarbon radical, and n is a number from 2 to 3.
In the following examples and description, we
' have set forth several of the preferred embodiments of our invention, but they are included merely for purposes of illustration and not as a limitation thereof.
Example 1 grams of dioleyl ether is blown with air at C. using copper naphthenate as a catalyst. When the specific gravity of the material has increased 0.07-unit 50 grams of phosphoric acid are added, the reaction mixture is heated on a the structure resulting from the blowing operato steam bath for 12 hours. The excess acid is removed by washing with water. The heavy viscous phosphated product that results is water soluble.
Example 2 100 grams of ethylene glycol diricinoleyl ether is blown as in Example 1 and reacted with 60 grams of phosphorous acid at 100 as above. The heavy viscous product is washed with water. The resulting phosphorous acid ester is water soluble.
Example 3 100 grams of propane-1,2,3,-tricrotyl ether is blown as in Example 1 until the specific gravity has increased 0.05-unit and then reacted with 50 grams tetraphosphoric acid as in the examples above. The excess acid is removed by Washing with cold aqueous salt solution. The product is soluble in water.
Example 4 100 grams of tetrahydrofurfurylerucyl ether are blown as previously described until the specific gravity of the oil has increased 0.04-unit and reacted with a 1:1 mixture of phosphoric acid and pyrophosphoric acid. The product is worked up as above.
While we have found it convenient to illustrate our invention by reference to procedures involving the blowing of certain specific unsaturated ethers, it will be evident that many modifications in such procedures may be made within the scope of our invention. In general, it may be said that irrespective of the particular ether dealt with, the blowing operation may be carried out in a manner strictly analogous to that which has been employed in the blowing of various oils, fats, and waxes for many years.
The compounds of our invention have many valuable applications in industry. For example, they may be employed as surface-active agents, wetting, washing and dispersing agents. We have found them to have outstanding properties when employed as lubricating anti-static and conditioning agents for textile yarns, particularly those composed of or containing cellulose acetate and related cellulose derivatives.
What we claim is:
1. The process of producing an ester of an acid of phosphorus which comprises blowing an unsaturated ether selected from those having the following formulas:
wherein R is an unsaturated hydrocarbon chain of 3 to 25 carbon atoms in which the unsaturation is limited to olefinic unsaturation and R is a low carbon atom saturated hydrocarbon radical, and n is a number from 2 to 3, at from 50 to 200 C., until an appreciable increase in specific gravity occurs, and thereafter treating She blown other with an acid of phosphorus selected from the group consisting of phosphorous, phosphoric, pyrophosphoric and tetraphosphoric acids.
2. The process of producing an ester of an acid of phosphorus which comprises blowing dioleyl ether, at from 50 to 200 C., until an appreciable increase in specific gravity occurs, and there after treating the blown ether with phosphoric acid.
3. The process of producing an ester of an acid of phosphorus which comprises blowing propanel,2,3-tricrotyl ether, at from 50 to 200 C., until an appreciable increase in specific gravity occurs, and thereafter treating the blown ether with tetraphosphoric acid.
4. The process of producing an ester of an acid of phosphorus which comprises blowing tetrahydrofurfurylerucyl ether,at from 50 to 200 C., until an appreciable increase in specific gravity occurs, and thereafter treating the blown ether with a mixture of phosphoric and pyrophosphoric acids.
JOSEPH B. DICKEY. JAMES G. McNALLY.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 1,944,530 Schonburg Jan. 23, 1934 2,185,967 Priester Jan. 2, 1940 2,200,299 Robinson May 14, 1940 2,241,244 Conary et a1 1.. May 6, 1941 2,260,819 Balassa Oct. 28, 1941 2,345,734 Dickey et a1. Apr. 4, 1944 2,372,244 Adams Mar. 27, 1945 FOREIGN PATENTS Number Country Date 452,508 Great Britain Aug. 24, 1936
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US602413A US2478377A (en) | 1945-06-29 | 1945-06-29 | Preparation of esters of acids of phosphorus |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US602413A US2478377A (en) | 1945-06-29 | 1945-06-29 | Preparation of esters of acids of phosphorus |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2478377A true US2478377A (en) | 1949-08-09 |
Family
ID=24411243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US602413A Expired - Lifetime US2478377A (en) | 1945-06-29 | 1945-06-29 | Preparation of esters of acids of phosphorus |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2478377A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2648696A (en) * | 1951-06-19 | 1953-08-11 | Shell Dev | Mixed acid anhydrides and process for production of same |
| DE952386C (en) * | 1954-02-05 | 1956-11-15 | Du Pont | Process for the production of polymeric organic phosphates |
| US2979523A (en) * | 1956-03-06 | 1961-04-11 | Gulf Oil Corp | Addition products of dialkyl acid orthophosphate and olefin oxides |
| US3341633A (en) * | 1955-01-27 | 1967-09-12 | Lubrizol Corp | Reaction of o, o-dihydrocarbyl phosphorodithioic acids with epoxides |
| US5707559A (en) * | 1986-07-17 | 1998-01-13 | Tropix, Inc. | Chemiluminescent 1,2-dioxetane compounds |
| US6322727B1 (en) | 1986-07-24 | 2001-11-27 | Tropix, Inc. | Kit for conducting an assay to detect a substance using enzymatically-induced decomposition of dioxetanes |
| US20050161415A1 (en) * | 2004-01-15 | 2005-07-28 | Iversen William W. | System for the storage and organization of clothing under travel conditions |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1944530A (en) * | 1929-04-08 | 1934-01-23 | Ig Farbenindustrie Ag | Phosphoric acid esters |
| GB452508A (en) * | 1934-01-24 | 1936-08-24 | Chemische Fabriek Servo Nv | A process of manufacturing washing, cleansing, wetting and emulsifying agents and treatment baths containing the same |
| US2185967A (en) * | 1936-01-15 | 1940-01-02 | Ind Mij Nv Deventer | Linoxin-like material and process of manufacture |
| US2200299A (en) * | 1939-04-13 | 1940-05-14 | Nat Oil Prod Co | Fatty alcohol derivative |
| US2241244A (en) * | 1939-03-25 | 1941-05-06 | Texas Co | Organic phosphite compound and method of manufacturing same |
| US2260819A (en) * | 1941-10-28 | Coating composition | ||
| US2345734A (en) * | 1939-07-18 | 1944-04-04 | Eastman Kodak Co | Self-emulsifying phosphated and phosphited oils as antistatic lubricants |
| US2372244A (en) * | 1941-09-24 | 1945-03-27 | Standard Oil Co | Esters of acids of phosphorus |
-
1945
- 1945-06-29 US US602413A patent/US2478377A/en not_active Expired - Lifetime
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2260819A (en) * | 1941-10-28 | Coating composition | ||
| US1944530A (en) * | 1929-04-08 | 1934-01-23 | Ig Farbenindustrie Ag | Phosphoric acid esters |
| GB452508A (en) * | 1934-01-24 | 1936-08-24 | Chemische Fabriek Servo Nv | A process of manufacturing washing, cleansing, wetting and emulsifying agents and treatment baths containing the same |
| US2185967A (en) * | 1936-01-15 | 1940-01-02 | Ind Mij Nv Deventer | Linoxin-like material and process of manufacture |
| US2241244A (en) * | 1939-03-25 | 1941-05-06 | Texas Co | Organic phosphite compound and method of manufacturing same |
| US2200299A (en) * | 1939-04-13 | 1940-05-14 | Nat Oil Prod Co | Fatty alcohol derivative |
| US2345734A (en) * | 1939-07-18 | 1944-04-04 | Eastman Kodak Co | Self-emulsifying phosphated and phosphited oils as antistatic lubricants |
| US2372244A (en) * | 1941-09-24 | 1945-03-27 | Standard Oil Co | Esters of acids of phosphorus |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2648696A (en) * | 1951-06-19 | 1953-08-11 | Shell Dev | Mixed acid anhydrides and process for production of same |
| DE952386C (en) * | 1954-02-05 | 1956-11-15 | Du Pont | Process for the production of polymeric organic phosphates |
| US3341633A (en) * | 1955-01-27 | 1967-09-12 | Lubrizol Corp | Reaction of o, o-dihydrocarbyl phosphorodithioic acids with epoxides |
| US2979523A (en) * | 1956-03-06 | 1961-04-11 | Gulf Oil Corp | Addition products of dialkyl acid orthophosphate and olefin oxides |
| US5707559A (en) * | 1986-07-17 | 1998-01-13 | Tropix, Inc. | Chemiluminescent 1,2-dioxetane compounds |
| US6322727B1 (en) | 1986-07-24 | 2001-11-27 | Tropix, Inc. | Kit for conducting an assay to detect a substance using enzymatically-induced decomposition of dioxetanes |
| US6514717B2 (en) | 1986-07-24 | 2003-02-04 | Tropix, Inc. | Kit for conducting an assay to detect a substance using enzymatically-induced decomposition of dioxetanes |
| US20030175838A1 (en) * | 1986-07-24 | 2003-09-18 | Bronstein Irena Y. | Kit for conducting an assay to detect a substance using enzymatically-induced decomposition of dioxetanes |
| US6913897B2 (en) | 1986-07-24 | 2005-07-05 | Applera Corporation | Kit for conducting an assay to detect a substance using enzymatically-induced decomposition of dioxetanes |
| US20050161415A1 (en) * | 2004-01-15 | 2005-07-28 | Iversen William W. | System for the storage and organization of clothing under travel conditions |
| US7143902B2 (en) * | 2004-01-15 | 2006-12-05 | Iversen William W | System for the storage and organization of clothing under travel conditions |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2563506A (en) | Quaternary ammonium salts of | |
| US3331896A (en) | Method of preparing alkali soluble phosphate esters of hydroxylic organic compounds | |
| US2478377A (en) | Preparation of esters of acids of phosphorus | |
| US2466393A (en) | Preparation of esters of acids of phosphorus | |
| US2329707A (en) | Metal organophosphates and method of preparing the same | |
| US3341633A (en) | Reaction of o, o-dihydrocarbyl phosphorodithioic acids with epoxides | |
| US3830886A (en) | Phosphorus compounds containing stable halogen | |
| US2234379A (en) | Preservation of soap | |
| US2336302A (en) | Hexaesters of tetraphosphoric acid | |
| US2488449A (en) | Organo-silicon-phosphorus condensation products | |
| US3919361A (en) | Polyfluoroalkyl hydroxypropyl phosphates | |
| US2386250A (en) | Phosphated blown oils | |
| DE2828603A1 (en) | NEW PHOSPHORUS COMPOUNDS AND THEIR USE IN FLAME RETARDANT COMPOSITIONS | |
| US2490748A (en) | Preparation of esters of acids of phosphorus | |
| US2121611A (en) | Naphthenyl esters of phosphorous acids | |
| US2466394A (en) | Preparation of esters of acids of phosphorus | |
| US3639539A (en) | Phosphorus-containing n n-dimethylolcarboxylic acid amides | |
| Sanin et al. | The effect of synthetic additives in lubricating oil on wear under friction | |
| US3254027A (en) | Lubricating oil compositions | |
| US3706822A (en) | Method of refining esters of organophosphorus | |
| GB821503A (en) | Polymeric compositions containing nitrilo methylol-phosphorus polymers and bromine | |
| US2862016A (en) | Process for preparation of alkali salts of o,o-thiolphosphoric acid asymmetrical diesters | |
| Hochwalt et al. | Alkyl esters of phosphoric acid | |
| US2676975A (en) | Process for production of phosphate esters | |
| EP0029172B1 (en) | Alkylphosphonic acid half-ester salts, their preparation and their use as sizing agents in textile fibres |